I know it's ridiculous, but I have a very hard time paying for software. I love being thrifty, but the bias that I (and I suspect many of you) have against paying for apps could is rarely worth it. Here's why.

Free software is great. You download it, install it, and get on with your day without a penny less in your pocket—in theory. The problem: While a lot of free software is truly great, there are a lot of free applications and tools out there that merely "get the job done", and sometimes they don't do it adequately.

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Meanwhile, commercial developers are creating wonderful apps that I (and many of you) completely ignore because they're charging a few bucks. Sure, this attitude hurts the software developers who want to make a living from developing cool software, but it also hurts us as users—because we often end up stuck with mediocre software as a result. When I actually pay for the few things that deserve my money, I can spend less time fiddling, clamoring for support, dealing with bugs, and cursing their names under my breath; instead, I can spend more time getting things done. (Shocker, huh?)

Note, before I begin, that this is not an argument against free software, nor do I think that these rules apply to every app out there. I love free software as much as the next guy (hell, I'm a Linux user for crying out loud). I think it's great that in today's world, you can make your life a bit easier with a quick, pain-free download. The point I'm trying to make is that a quick, pain-free download that leaves you with a couple fewer bucks in your pocket can often make your life a lot easier. We need to judge these things on an app-by-app basis—if the free alternative is just as good or better, go with it. But we don't need to ignore pay apps just because they cost money.

Commercial Software Often "Just Works"

The fact of the matter is that a lot of free apps out there require a bit of setup on the user's part, and even then don't always work as well as you'd hoped, while their paid counterparts are often stable, plug-it-in-and-go deals. It makes sense, if you think about it—if a developer is going to charge money for an app that anyone can make, they better make it the easiest damn app around.

PDAnet, a popular tethering app for a lot of mobile devices, is a great example of this. The full version of PDAnet is $25, but there are a few free options out there as well. The problem is, most of those free options require some configuration to use—in fact, many require you to root your phone first, something that, while easy nowadays, many people still prefer not to do. So, you could go the free route, which takes a lot of work before you're up and running, after which it might not even work that well. On the other hand, a one-time payment of $25 (which, let's be honest—is a small price to pay for having internet anywhere), you can be up and running with just a few clicks.

Commercial Software Normally Has Great Support

One of the few apps I splurged on this year is previously mentionedPostbox, an incredible email client for Windows and OS X. Apart from just being plain better than Mail.app on the Mac, one of the things I've come to love about Postbox is the incredible support from the developers.

Postbox is developed by a small group of coders, but because they get paid for their program, the two founders are incredibly helpful in the support forums. Not only will they respond to nearly every user question, but they really listen to their users when adding features to upcoming versions of the app. That's not to say that free software can't have great support, but in my experience—especially with small developers—I've been hard-pressed to find commercial software that didn't measure up to my expectations as a paying customer. Sometimes, with free software, it's a crapshoot as to whether anyone will listen to your input or help you fix your problems. When someone's competing for your business, they have a lot of reason to listen to what you have to say.

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Another great example are DVD ripping applications—sure, free apps like DVD Shrink often get the job done nicely, but as the movie companies come out with newer and better encryption methods, some free apps fall behind. Pay apps like Lifehacker FavoriteDVDFab are able to stay on top of those encryption methods and update their software to support even the newest DVDs.

Commercial Software Often Makes It Easier to Get Things Done

Not only does that competition allow for great service, but it really motivates developers to create something useful, that hasn't been done before. Postbox fits pretty well into this category too, with features like Gmail-caliber searching, file and attachment organization, and threaded conversations that put Mail.app's to shame. It's hard to ignore real, hard features like this that actually make you more productive.

Another example is Remember the Milk's freemium model; it's free for basic service but has a Pro subscription available that, among other great perks like priority support, allows for use of the official mobile apps. That alone seems reason to plop down some cash—especially when all other mobile RTM-syncing apps are, in my experience, riddled with bugs. (Astrid, for example, is a free Android app that syncs with Remember the Milk, but still starts creating duplicate tasks after a few days, and for the longest time would just not follow the notification rules available in the settings). When it comes to apps that literally drive my productivity, I'd rather pay a few bucks to the good developers than use a buggy, unreliable solution.

Sometimes, the Free Alternatives Just Plain Suck

It's unfortunate, but sometimes, certain categories of apps are complicated enough that free options just won't cut it. While Android has great GPS and turn-by-turn navigation software built-in (in the form of Google Maps Navigation), for example, iPhone users aren't nearly as lucky. Sure, there are a few free apps out there, but to be completely honest, they're not very good. You're a lot better off paying a one-time fee for something like the well-doneTomTom, or paying for a subscription to the greatMotionX GPS Drive if navigation is important to you. Again, it can get a bit costly, but if you shop around, you should be able to find a good app for a decent price. Besides, buying a separate GPS unit—whether it's a handheld Garmin or one built into your car—costs a heck of a lot more than the $60 it costs to get TomTom on a device you already have. In the end, if it's something you use a lot, you're going to be better off going with the app that works best, even if it is a few bucks more.

Another great example is the instant messaging scene on Android. The awesome Trillian client just came out of beta, and it's a fantastic app—yet every other blog on the net complained about how it isn't worth the massive price of $5, as if you couldn't scrounge up five bucks under your couch cushions (or skip buying another coffee). It's already the best IM client available for Android, and in my experience, is far more reliable than the other constantly-disconnecting free options out there.

Sometimes, Free Just Isn't an Option

It's a bit rarer, but sometimes those Holy Grail-type apps are just one of a kind—like Air Video for iOS (possibly the best $3 we've spent in the App Store). It streams videos to your iPhone with minimal effort, converts them on-the-fly for the best viewing experience, and will even stream over 3G when you're away from home. And, it's incredibly easy to use—so even when other apps start cropping up, it'll probably still be worth paying for because it just works.

We focus a lot—in fact, almost exclusively—on free software here at Lifehacker, but that doesn't mean we don't think some programs are worth our hard-earned cash. When it comes to the things that are important to your day-to-day life—whether it's staying in contact with your friends over IM, productively sifting through email, managing your to-do list, or just getting where you need to go—sometimes loosening the purse strings can do you a lot of good.

Some of you may seriously disagree with me on this (while I'm sure others of you are right with me), so let's get some discussion started. Share your thoughts with us in the comments.